Phenoxyacetohydrazide Schiff Bases: β-Glucuronidase Inhibitors
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Compound No. | R1 | R2 | Yield (%) | Compound No. | R1 | R2 | Yield (%) | ||
---|---|---|---|---|---|---|---|---|---|
1 | H | 81 | 15 | H | 88 | ||||
2 | H | 85 | 16 | H | 92 | ||||
3 | H | 93 | 17 | CH3 | 94 | ||||
4 | H | 87 | 18 | H | 89 | ||||
5 | H | 83 | 19 | CH3 | 87 | ||||
6 | H | 86 | 20 | H | 84 | ||||
7 | H | 89 | 21 | H | 94 | ||||
8 | H | 91 | 22 | H | 93 | ||||
9 | H | 94 | 23 | H | 91 | ||||
10 | H | 82 | 24 | CH3 | 95 | ||||
11 | H | 88 | 25 | H | 91 | ||||
12 | H | 91 | 26 | H | 88 | ||||
13 | H | 86 | 27 | H | 81 | ||||
14 | H | 93 | 28 | H | 93 |
2.2. β-Glucuronidase
Compounds | IC50 (μM ± SEM a) | Compounds | IC50 (μM ± SEM a) |
---|---|---|---|
1 | 9.20 ± 0.32 | 15 | 12.0 ± 0.16 |
2 | NA b | 16 | NA b |
3 | NA b | 17 | NA b |
4 | NA b | 18 | NA b |
5 | 9.47 ± 0.16 | 19 | NA b |
6 | NA b | 20 | NA b |
7 | 14.7 ± 0.19 | 21 | 13.7 ± 0.40 |
8 | 15.4 ± 1.56 | 22 | 22.0 ± 0.14 |
9 | NA b | 23 | NA b |
10 | NA b | 24 | NA b |
11 | 19.6 ± 0.62 | 25 | NA b |
12 | 30.7 ± 1.49 | 26 | NA b |
13 | NA b | 27 | NA b |
14 | NA b | 28 | NA b |
D-saccharic acid-1,4-lactone c | 48.4 ± 1.25 | - | - |
3. Experimental
3.1. General Information
3.2. Biological Assays
3.3. Assay for β-D-Glucuronidase
3.4. Typical Method for the Synthesis of Compounds 1–28
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Jamil, W.; Perveen, S.; Shah, S.A.A.; Taha, M.; Ismail, N.H.; Perveen, S.; Ambreen, N.; Khan, K.M.; Choudhary, M.I. Phenoxyacetohydrazide Schiff Bases: β-Glucuronidase Inhibitors. Molecules 2014, 19, 8788-8802. https://doi.org/10.3390/molecules19078788
Jamil W, Perveen S, Shah SAA, Taha M, Ismail NH, Perveen S, Ambreen N, Khan KM, Choudhary MI. Phenoxyacetohydrazide Schiff Bases: β-Glucuronidase Inhibitors. Molecules. 2014; 19(7):8788-8802. https://doi.org/10.3390/molecules19078788
Chicago/Turabian StyleJamil, Waqas, Shagufta Perveen, Syed Adnan Ali Shah, Muhammad Taha, Nor Hadiani Ismail, Shahnaz Perveen, Nida Ambreen, Khalid M. Khan, and Muhammad I. Choudhary. 2014. "Phenoxyacetohydrazide Schiff Bases: β-Glucuronidase Inhibitors" Molecules 19, no. 7: 8788-8802. https://doi.org/10.3390/molecules19078788